Pillow Talk 24

Me and my wife were dating at the time. After a good night, both of us spent, I asked a question that would change our relationship until this very day. I was 23, she was 18. She was slim, 5'3", maybe 100 pounds, 34b breasts, with a teardrop ass that was amazing. Long dirty blonde hair that reached her lower back. Snuggling with her, I asked her what was her most secret fantasy. I had to ask a few times, I think because she feared my reaction. Assuring her, no matter what it was, it was only a fantasy. She finally admitted, she wanted a MFM threesome. Then she asked mine. Almost instantly, I answered, FMF threesome. She related, she would not want me to have such a fantasy come true. She couldn't handle herself seeing me with another girl. When I told her, the love I had for her, me being a lil older, not wanting to rob her of her youth, and if we were to be together, I didn't want her to have any regrets. I didn't want her, later down the road, to blame me for anything she would have missed out on. I would help to make any and all of her fantasies come true.

The conversation dwindled down, but stayed in my head. Over the next couple of months, I would bring the subject up while having sex with her. It was to the point where she was avoiding any answers to my questions, and I would tease her by stopping or slowly pumping her, going deep, waiting a few seconds, before doing it over and over, driving her crazy, waiting for an answer. It was great sex, but I could only imagine how much she would be into having to take care of 2 guys at one time. Asking her if she really wanted to try it, her, delaying an answer, then finally the words passing her lips that she really wanted to. Only then, I would pump as hard, deep, and fast as I could and blow my load. Every session, more details would emerge of what she really wanted. It was a part of our love making. More pillow talk, was all the things I had asked, the answers she had given, she finally asked if I was serious about the scenario. Of course I was, I had no idea how to make it happen, but I would be ok if it did.

Asking her, who she had imagined doing this with, she said she didn't want to choose a guy, that I may read more into that than there actually was. She said she wanted me to find a guy for her. To let her know who, and she would let me know if she would be ok with him. So, the wheels were turning. Who can the guy be? A friend? A stranger? The thought of a stranger didn't strike me as a good choice. The thought of a friend, it was the same thoughts. How do I ask a guy that I want him to join me doing my girlfriend? I decided a not so close friend. Someone I knew, almost a friend, but not. Asking a real friend, could ruin a friendship if he wasn't into that. Asking a stranger felt it would just be creepy. Someone I knew, but not close, his reaction wouldn't have been a big deal if he refused. And I could have played it off like I was joking with him.

In the following couple of weeks, she would ask if I found someone yet. The pressure was on. I finally confided with my boss. He wasn't a real friend. He knew something was up with me. Lack of concentration on my work. I told him what was going on with me and my girl. Telling him, asking him not to judge, I thought me confiding would make our friendship better. Expecting advice, even consultation went right out the window when he said he would fuck her, and I wasn't expecting that answer. He was 39yrs old, married. I didn't consider asking him to do anything before. Since he offered, I saw him in a different light. I wasn't sure if my girl would allow a guy more than twice her age fuck her. She had met him a few times. So she knew who he was, what he looked like. He was always polite to her. My boss told me to tell her he would love to fuck her.

That night, I brought the subject up and hinted I had a prospect, she asked if I found someone. I asked her what she thought of my boss. She was shocked, not thinking I was serious. She did say she thought he was handsome, but married. That he wouldn't want to do such a thing. I said nothing. Thinking it would have to be a surprise for her. The next day, she was staying at my apartment when I went to work. I would be at work for the lunch shift. I would be back in a few hours. At work, my boss pulled me in his office, and asked if I told her. I told him what she said. I told him, too bad he would be at work all day, cuz we could go surprise her when I got off work. He reminded me, he was the boss, and that day was the day. He was gonna visit, try his luck, and if it didn't work out, it was all good either way.

Bout half an hour before I was scheduled off, he told me I could go home, and he would show up a short time after. I got to my apartment, giving my girl lots of attention, thinking of the possible things that could happen if he showed up. A knock at the door, I open, there is my boss, I invited him in. He joined us at the table. He asked for alcohol, all I had was a bottle of tequila. Me and him did a cpl of shots. He was complimenting my girl on how good she looked. Saying how sexy she must be when naked. My girl was shy, kinda laughing it off. My boss suggested we play poker, no money, but clothes instead. My girl refused. He started shuffling and dealing cards while she kept saying no way. He said he would make it super fair for her, he took off his shoes, socks, pants. Standing in front of her, just his shirt and boxers. I saw her staring at his bulge before he sat back down. She agreed to play.

I was the 1st one to loose my clothes. He still had his boxers. She still had her panties, bra, and shirt. She lost another hand and didn't want to take her shirt off. He got up and took her shirt off for her. She couldn't help but stare at his junk in his boxers while he took her shirt off. He lost the next hand and asked if she would help him out of his boxers. She refused. So he stood up, pulled them down and he had a huge dick. My girl asked him how big it was. He said 9 inches when it gets hard. He had lost so the game changed from strip poker to dare poker. Since me and my girl were still playing, he had me take her bra and panties off. He had us make out, he had her stroke my dick, had me suck her nipples. Had her suck my dick, not very long at all, until the next hand was dealt. I finally won a cpl hands, had him suck her nipples, had her stroke his dick, when I tried to have her suck his dick, she wanted to quit. She got up and went lay down in the bed. I followed. Was kissing her and playing with her tits. I went to start playing with her pussy, and start fingering her. That's when I noticed, he was in the bed with us. He already had a cpl fingers in her pussy. I nudged him away so I could start eating her out. He was good with that, he knelt on the bed by her head so she could suck his dick. I know she came, she squirmed her body and pushed my head away from her.

That was his que to nudge me out the way. He got between her legs and put his dick in her. A little at a time for bit, it wasn't long until he was balls deep in her. She was taking all of his 9 inches, she was moaning with every thrust he was giving her. I knelt by her head so she could suck my dick. It muffled most of her moans. She would stop sucking me often to moan out load while catching her breath.

It was only a few minutes for me until I came on her neck and chest. I was then kinda stuck to watch him fuck my girl like I never could. For like 15 minutes. Then hearing him grunt a few times and see his motions stop. Staying motionless on top of her for a minute. He pulls his dick out of her. A string of cum stretching from her pussy to the tip of his uncut cock.

He gets up. She just laid there, eyes closed, breathing hard, legs still open. I move to get a better look, her pussy had a gaping hole and cum was starting to ooze out in slow spurts. Before I knew it, he had his clothes back on, and leaned over the bed to kiss her on the forehead. She finally opened her eyes. He thanked her, and said he had to get back to work. He left us.

Me or my girl didn't say much after. I laid next to her holding her. She fell asleep. I was wide awake, trying to process what had happened. There was plenty of afterthoughts. It was the next night before me and my girl talked about what happened. She was ok with it. I didn't have the strength to tell her I wasn't at that time. I have come to terms that whatever makes her happy makes me happy.